When Dean got home, Sam was dressed in a t-shirt, baggy green and white plaid flannel pants and socks, sitting on the living room couch and staring blankly at the TV. Dean closed the door behind him, shrugged out of his coat and held it in his hand as he stood awkwardly in the doorway staring at his brother.

"Hey Sammy, I'm home."

When Sam turned towards him, his eyes were dry but red and puffy and his cheeks were shiny; he'd obviously been sobbing for a while. He gave Dean only the briefest glance and then looked down at the couch, then back to the television for a second, as if he didn't care that he was home. "Hey Dean." Fidgeting uncomfortably under Dean's stare, it was pretty apparent that Sam was only pretending to watch television and after a minute, he picked up the remote, shut off the television, sighed, and stood up. "I'm gonna go to bed, I guess I'll see you in the morning."

"Sam, wait." Dean quickly walked across the room and stood in front of Sam, then threw his jacket over the armrest of the couch behind him. "Sam, I'm sorry."

"Me too," he mumbled. "I shouldn't have sprung it on you like that. I just…I don't understand. I thought –" his voice broke and he looked down and away, but Dean could still see the few new tears wetting his face. "I thought you'd want to."

Dean quickly reached up, grabbed Sam's face, and turned it towards him. "Hey – hey – hey – hey, Sammy" he rubbed his thumbs across Sam's cheeks, wiping the tears away and smearing the shiny, wet tracks. "Sammy, look at me, look into my eyes. I do want to, so much. I'm sorry; I know I was being a major dick earlier, I shouldn't have run out like that. I just needed some time to think. But I do want you; don't ever think I don't. Look into my eyes and tell me if I'm lying."

Sam's solemn eyes searched Dean's for a moment. He nodded and then wiped an arm across his face, completely clearing off any moisture lingering there, and sighed. "Well, I guess if you want us to wait a while, I can do that. But whenever you think is a good time, well, I'm ready whenever you are."

Dean took his hands away from near Sam's face and put them awkwardly to his sides. He thought about what he wanted to say next and suddenly felt stupid and clumsy. He didn't know how to speak or where to put his hands, his heart raced and he felt a lump forming in his throat like some virginal pre-teen. "How about now?"

Sam's eyes grew wide and his mouth dropped open. "Really? Are you sure? I don't want you doing this just for me if it doesn't feel right to you."

Dean took another step into Sam's space so that their faces were only inches apart. "Do you want this, Sam? Are you absolutely sure you want your first time to be with me?"

Sam nodded. "Yeah, Dean. I'm sure."

"Then I'm ready."

Sam stood still for a moment, looking thoroughly shocked and unsure of what to do next. Then, shyly, tentatively, he reached out and stared at his hand as he rubbed it up and down Dean's bicep. "Okay, well, uh…"

He leaned in slowly, closed the three or four inch gap between their faces and kissed him. It was slow, unhurried, and felt as unpracticed and awkward as if it was the first time Sam had ever kissed anyone. Dean moved his experienced mouth against Sam's, trying to lead the kiss and help Sam's lips get into a rhythm, but he couldn't help the excited tightening in his throat and stomach that made him feel like he was a little off his game. When getting ready for sex he was used to feeling excitement, but it was never like this; he never felt awe, or love, or this stupid nervousness he had in his hands that he wouldn't be able to touch Sam right, or the strong anxiety he felt over not being able to satisfy him properly. As they kissed, he put his hands experimentally at the sides of Sam's waist and pulled him in so their bodies could touch and then Sam followed suit, shyly touching Dean the same way. Dean broke the long kiss, gave him a couple more pecks on the lips, and then laid a soft, gentle kiss on the little mole beside Sam's nose.

"You wanna take this to the bedroom, or you wanna have sex on the couch?"

Sam blushed. "Bedroom."

"Okay." They disentangled themselves and then Dean grabbed Sam's hand. "Come on," he whispered and then tugged, leading them to the bedroom.

When he opened the door and pushed inside, the room was unlit, save for a lamp beside the bed that cast dim light and shadows around the room. There were two beds in the room: Sam's, which was in the far left corner and almost always made because it was rarely slept in, and his, which lay right in front of them, unmade and with the condoms and lube still sitting in the exact same place they had been when he'd left. Beside the bed, all of Sam's clothes, save for the t-shirt he was wearing, were still on a crumpled heap on the threadbare carpet. Dean quickly threw off his boots and then heard the sound of the door clicking as Sam closed it behind them. Sam walked around him and then stood facing him at the foot of the bed, his eyes wide and a little scared looking, but his erection still tenting his pants noticeably as he lifted his shirt over his head and threw it to the ground. Visibly trembling fingers then reached down and grabbed the waistband of his pants, but Dean walked over to him and put a hand over Sam's, stopping him.

"It's okay, Sammy." He leaned in and gave Sam a comforting, chaste kiss on the mouth. "You don't have to get naked for me right away; we can go as slow as we want tonight."

"Yeah, I know, I'm sorry Dean, I'm just so nervous."

"I know. I am too."

Dean slipped his own shirt over his head and threw it to the ground next to Sam's. His eyes went wide in awe as he dragged them up and down Sam's lean, lithe, slightly trembling body. He slowly and uncertainly put his hands on the sides of Sam's waist. This shouldn't feel so awkward to him; he'd had sex before, loads of it, with a lot of different people. More than that, he'd messed around with Sam so many times already, going much further than just touching each other with their shirts off. But this was different; he was about to make love to Sam – his brother, his best friend, his partner in everything. Nothing he'd ever done was even remotely like this. He craned his neck forward and slowly licked Sam's lips and Sam responded instantly by leaning in and beginning to chase his mouth. Their mouths slid together and soon found a slow rhythm, working in time with one another as they sucked on each other's lips and tongues. Dean pulled Sam's body in towards him and Sam willingly stepped in to him so that the smooth skin of their chests could touch and then Dean moved his hands slowly up and down Sam's back in a comforting way, hoping to help calm his brother's nerves. Sam's hands were gliding up and down Dean's biceps, but then moved slowly down his sides and to the waistband of his jeans. Fingers dipped just barely inside and felt along the v-cut of muscle above his hips, then travelled along the waistband to the front of his jeans and felt along the thin line of fine, blond hair there. In the next moment, Dean's erection felt less restricted in his pants as Sam undid the button and zipper. Sam seemed more self-assured and he was no longer shaking, but his movements were still tentative and slower than usual and it seemed pretty clear to Dean that he needed to take the lead. He pushed on Sam's chest and Sam let himself fall backwards onto the bed, his feet still planted on the ground. Dean climbed on top of him, straddling his hips, and as Sam's serious and aroused face looked up at him, his longish hair making a messy circle around his head, Dean reached up and stroked his fingers along Sam's jaw.

"God, look at you, so gorgeous." He moved in and licked along Sam's lips, then looked down at his brother. "I love your body, Sam." He ran his hands across the hard, muscular planes of Sam's pecs, down to the hard ridges of his stomach, briefly touching the tip of the hot, hard bulge in his pants, then back up to his chest where he pinched each of Sam's nipples between his thumb and forefinger and then tweaked them just a little. "You're so fucking hot for me."

He moved his mouth to the side of Sam's jaw and opened his mouth wide to lay a kiss at the sensitive flesh and then sucked lightly and licked, inhaling the clean smell of Sam's skin and feeling his slight stubble under his tongue. "I am," Sam whispered, "want you so much –" Dean nipped the skin and Sam made a little moan and then hissed, "No hickies," in a raspy voice.

Dean nodded against Sam's skin. He actually suspected that Sam would like his skin to be sucked and bitten just enough to give him a few bruises, so it was really more of a reminder than anything, cautioning him about what he already knew: they couldn't leave any marks or signs of what they did to each other. He moved his mouth down the side of Sam's neck and over his smooth chest and stomach, slowly licking, kissing, and nibbling the smooth skin and little scars along the way. He loved giving Sam such elaborate attention and getting to hear his breath quicken, then come out in little gasps and pants as he thoroughly licked and sucked every part of his chest and stomach. When he got to the waistband of Sam's pants, he had to get off the bed and kneel in front of Sam on the floor. Sam spread his legs to accommodate Dean between them and once he was settled, he saw that the very tip of his hard, red head was peeking out from underneath the waistband and a small puddle of clear, slippery pre-cum was collecting on his stomach. Mm, no underwear. He grabbed Sam's pants and tugged, thoroughly enjoying the way Sam eagerly arched his back to make it easier for him. Once they were pulled down over his hips, he could see Sam's fully hard, flushed cock resting against his stomach. He grabbed it, lifting it away from the slick pool collecting on his stomach, and then brought it close to his mouth, where he could smell the strong musky odor of pre-cum that still leaked from the head. As he touched his tongue to the head, he looked up and saw Sam watching him and then their eyes locked as he moved his hand in a circular motion, rotating Sam's cock around his tongue.

Sam's eyes burned bright and his cheeks flushed as he watched. "Oh yeah, god Dean, you look so hot like that." Then Dean jammed his tongue into the slit and Sam's body began to shake and he threw his head back and let out a filthy moan. "Ooh – god – Dean…"

"What is it, Sam? You want me to suck your dick?"

In response, all Sam seemed to be able to do was let out an unintelligible moan that sounded so hot and needy, it made Dean leak a little pre-cum into his boxers. Dean took his tongue off of Sam but kissed the head and then opened up and felt the velvety-soft skin slide past his lips and into the hot, wet heat of his mouth. He wrapped his hand around the base and jerked him in time to his mouth as he bobbed slowly up and down Sam's cock, making his lover moan, thrash on the bed, and grab handfuls of sheets. And, like when he'd done this before, it wasn't long before Sam's hands were on his head, tangling in his hair, and trying to push him off.

"Stop! Dean, stop – oh – oh god – stop!" Dean pulled back and Sam was instantly covering his hand on the base of his cock, squeezing hard to stop his orgasm. "Oh god, that was close."

"You don't want me to make you come?"

Sam shook his head. "Not yet. I wanna wait until we're…well, you know."

If Dean wasn't so turned on at the time, he might have actually laughed at Sam at that moment. The kid was minutes away from having sex and still couldn't say the word out loud. "Are you sure? I'll bet I can make you come twice."

"I'm sure."

"Okay." Dean crawled back up on the bed and gave Sam a quick kiss on the mouth. "Are you ready?"

Sam nodded. "Definitely."

Sam's hands reached down to Dean's pants and gruffly pushed them and his boxers down over his thighs, but then Dean got up off the bed so he could take his pants and boxers down the rest of the way and slip off his socks. Then he went to the foot of the bed, grabbed the waistband of Sam's pants and pulled them the rest of the way off, then took off his socks for him one at a time. He looked down at Sam's fully naked body; the muscular legs, his red, straining erection, his smooth, young skin that looked a little orangey under the soft glow of the lamp and was covered in a thin sheen of shiny sweat, his soft, pink lips, his wanting, pleading, trusting eyes. Sam wanted this, he wanted him, and he trusted him to make it good for him. Dean leaned over Sam and grabbed the condoms and lube from where they still lay on the bed above Sam's head and then stood back up.

"Turn over for me."

Sam immediately did as he was told, getting on his hands and knees and then he crawled up the bed, towards the headboard, to give Dean some room to get behind him. Dean got on his knees behind Sam, set the box of condoms beside them, and opened the bottle of lube.

"I have to prepare you to make sure I don't hurt you, okay?"

"Yeah, I know. Do it."

Dean blinked in surprise, but only for a second. Yeah, of course Sam knew what to do; like everything else, the kid had probably researched to death all about how to have gay sex during the past several weeks before approaching him about it. He wondered if Sam went to an educational website or if he just watched some gay porn to figure it out. Dean leaned in and laid a line of kisses down Sam's lower back and then playfully nibbled one of his butt cheeks. Maybe he'd ask later and find out what else Sam knew. He squirted a generous amount of lube onto three of his fingers, then brought his forefinger to Sam's entrance and began petting around it, seeing how the muscles began to twitch and contract under his touch. He kept rubbing for about a minute until Sam started to moan and the muscles began to pulse and spasm. Oh god, he wanted to be inside Sam's ass so fucking bad, he could hardly stand it. He pushed his finger in all the way to the webbing and then began to slowly move it in and out. The muscles felt tight, but Sam didn't seem to feel any discomfort; instead, he rocked back on his finger.

"Mm, Dean, I'm ready, put another one in."

Dean raised an eyebrow. "Done this before?"

Sam hesitated. "Tried it a little the last couple of weeks."

He thought about Sam kneeling on their bed alone and fingering himself and, fuck, it made him so hot that he actually growled. "Really? Oh fuck, that is seriously hot. Watching you do that to yourself is so going on the 'To-Do' list for later."

He pulled the first finger out and then watched in wonder and curiosity as two of his slippery, wet fingers disappeared inside of Sam's body. Sam's muscular walls tightened up around them and he heard him stifle a little groan, so he stilled his fingers and let him get used to the girth and ran a soothing hand along Sam's back.

"It's okay; try to relax."

When he felt the muscles loosen around his fingers a bit, he began sliding then in and out and then moved them in scissoring motions to open up Sam further. At first, Sam stayed perfectly still and held his breath as he moved, but after a couple of minutes began rocking back and forth on his fingers, his moans growing increasingly loud and urgent. "Oh god – I'm ready, take your fingers out, I wanna face you."

"Fuck! I want to, Sam, I want to so fucking bad." He kissed the middle of Sam's back, along his spine. "Just take one more first; I don't wanna hurt you, babe."

When Dean added the third finger, he moved them gingerly, moving the tips just a little bit and changing the angle ever so slightly every once in a while. He'd heard about a spot that guys had deep inside them that would make Sam feel really good if he could find it.

"Dean! God, Jesus Christ, I'm ready! Please!"

Sam hadn't shuddered or shown any signs that he'd hit anything special inside of him; he was just impatient and wanted to have sex. And so did Dean; his cock was leaking so much pre-cum that there was a thin string of it connecting the head of his cock to the bedspread underneath them. He pulled his fingers out and wiped them on the bedspread and Sam flipped himself over so that he was lying on his back and facing him, his cheeks flushed and his cock so hot, hard and swollen that it looked like he was about to come any minute. Dean opened the box of condoms, then took out a strip of them, ripped one off and tossed the box to the floor. Once he had the condom rolled all the way down to the base, he drizzled a little more lube onto it and then inched forward on his knees into Sam's space. He picked up his legs and put them on either shoulder, grabbed Sam's ass, firmly gripping a cheek in each hand, and lifted his pelvis in the air. Sam's breath hitched and when Dean looked up into his little brother's face, he saw that he was once again looked wide-eyed and scared.

"Sammy? You okay?"

"Y-yeah, I'm fine."

"Are you sure? We don't have to do this; if you want to stop, just say the word. I promise, I won't get mad or anything."

Sam closed his eyes, nodded, and took a deep breath. "I know. It's a little scary, but I want to. Go ahead, put it in."

Dean leaned forward and gave Sam a soft, reassuring kiss on the mouth, then sat up on his haunches, lined himself up, and slid forward. As he felt the head push past the first ring of muscle, he closed his eyes and let out a soft moan. Fuck, he was tight, so much hotter and tighter than any woman he could remember sleeping with. He moved forward inch by inch letting Sam slowly adjust until he was all the way inside, buried to the hilt, and then stayed completely still, although it took all his willpower not to move. Even with the condom, just being inside of Sam and feeling the muscles gently squeeze his cock felt amazing. Sam stared up at him and nodded his head, giving him the go-ahead to move. At first, Dean slid out slowly, not daring to move too much and then slowly eased himself all the way back in. More than anything, he was terrified of hurting Sam by moving too fast or pushing in too hard and he didn't want to mar Sam's memories of his first time by causing him any pain.

But Sam, however, didn't seem to have the same concern. After about five minutes, he pushed himself down hard on Dean's cock. "Faster!"

Dean began sliding out a little further, pushing in a little harder, and moving a little faster. And, damn, did it feel good; Sam was plenty slick from all the lubrication and he felt hot, tight, and fucking perfect around him. Sam screwed his eyes shut and made little grunts of pleasure and his hard cock twitched against his belly and leaked pre-cum over the already sticky skin. Seeing Sam enjoy it so much practically pushed Dean over the edge and before he knew it he was pushing into him faster, harder, rougher, and babbling all sorts of dirty things.

"Jesus Sammy, you feel so fucking good, you're so tight, so goddamn perfect, better than any pussy I've ever had, fuck, you're gonna make me come so fast and hard inside you –"

Surprisingly, the more Dean talked, the more worked up Sam got. His breathing became heavier, his moans louder, and then he used his arms to brace himself and started pushing his ass down harder on Dean's dick. Dean felt himself start to get close. He started changing the angles of his thrusts, still looking for that spot inside Sam that would make him –

"Oh my god!" Sam screamed out and arched his back on the bed. "What was that?"

"Looks like we found your sweet spot." Dean kept moving at the same angle, making sure to hit the same spot over and over again with each thrust, feeling proud of himself for finding Sam's prostate the first time they had sex and loving the filthy moans Sam made as he thrashed and grabbed onto everything he could, including bed sheets, the headboard, and Dean's knees. He felt his orgasm quickly rising within him and knew that no matter what he did, he wasn't going to be able to delay it for much longer.

"Shit, I'm so close, Sam. Can you come just like this, just with my cock? I know you can, I know you're so fucking close. Wanna watch you mess yourself up, just for me, just because I can make you feel so good this way."

Sam arched his back, made a loud, unintelligible noise, and came all over his chest and stomach and just the sight of that alone had Dean coming hard and fast, filling up the condom just a few thrusts later. After he felt the last satisfying tug of his orgasm, he carefully grabbed the base of the condom, gently eased himself out of Sam, then tied the condom off and threw it into the nearby trash and, still panting, collapsed onto the bed beside his lover. Sam brought the corner of the bed sheet to his chest and stomach and wiped it off, then turned onto his side, threw and arm over Dean, and kissed him on the side of the mouth. Dean turned his head towards Sam and then his body followed, throwing an arm over his lover and bringing him in close.

He laid a kiss on Sam's lips and then Sam turned back onto his back and stared blankly at the ceiling. "I'm not a virgin anymore."

Sam's face was expressionless and his voice was flat and toneless and Dean raised himself up on one elbow to get a better look at him. "Any regrets?"

Sam turned to him and grinned. "Hell no. I just still can't believe it, feels a little unreal." He laid still for a moment, looking deep in thought. "Hey, Dean, can I ask you a question? What changed your mind?"

Dean turned leaned over, turned off the lamp and laid back on the bed. "Goodnight, Sam."

They laid in the dark for a few minutes and then, "Dean?"

"Yeah?"

"Can we do it again?"

"Now?" Fuck, he remembered what it was like being a horny teenager, but that round of sex they'd just had was long and exhausting. And Sam's first time…sure, he was gentle, but the kid had to be sore.

"Uh, no, I meant, well…ever?"

In the dark where Sam couldn't see, Dean smiled. "Yeah, Sam, whenever you want; I'm ready whenever you are."

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